


Halloween Shenanigans

by myrandomnesslife



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Barebacking, Bottom Stiles Stilinski, Crossdressing Stiles Stilinski, Episode: s03e16 Illuminated, Halloween, M/M, Nipple Play, Underage Drinking, mentions of Season 3B, switching POV
Language: English
Status: Completed
Published: 2013-11-13
Updated: 2013-11-13
Packaged: 2018-01-01 10:26:26
Rating: Explicit
Warnings: No Archive Warnings Apply, Underage
Chapters: 1
Words: 4,127
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1043715
Author URL: https://archiveofourown.org/users/myrandomnesslife/pseuds/myrandomnesslife
Summary: <blockquote class="userstuff">
              <p>"We need to get this stupid thing off of you," Derek groans, pointing towards the corset Stiles is squished into. It’s red and black, with lots of fabric and lace with little bows.</p>
            </blockquote>





	Halloween Shenanigans

**Author's Note:**

> beta'ed by my bb [ breakingjen](http://www.breakingjen.tumblr.com)
> 
> this started off as an idea that I sent David. [ Here](http://sadiabloslikeithot.tumblr.com/post/62857733130/okay-so-you-know-how-were-supposed-to-be-getting) and it really inspired me, so the words just kept flowing and flowing until it turned into this.  
> <3

It’s Halloween and Stiles had decided to dress up in drag and go to Jungle to hang out with the Drag Queens. It’s not as though he wasn’t having fun with the Queens, but he decided to go back to the party that one of them started at Derek’s loft (while Derek was away). Stiles had been drinking some and a few guys felt him up a little, in the throng of people, gyrating bodies, Stiles stumbles, walking to the bathroom (he suddenly can’t remember where it’s at), _Does Derek even have a bathroom?_ Stiles thinks. The place is extremely crowded and he can’t see, the alcohol clouding his vision. He runs into Derek. Derek catches him before he brains himself on the staircase or the floor, which by the way Stiles was wobbling back and forth would be at any time if not for Derek.

Derek hadn’t intended to be back during Halloween, but he was and he saw all these asshole kids in and around his loft and he was furious. At first, but when he walked into the loft and went back towards the spiral staircase he saw Stiles lingering there, not at all aware of his surroundings or so it looked and he just can’t stay mad. At least _not_ at Stiles. He’d missed him, probably more than he’d ever care to admit.

"Der—" Stiles slurs, breathing on Derek’s face, the stench of alcohol overwhelming Derek’s nostrils. Stiles hangs his right arm on Derek’s shoulder lazily. He feels weird. "I miss—hiccup—you."

Derek laughs, holding Stiles up in a stronger grip. “I’m right here.”

"No." Stiles manages before hiccuping some more, trying to use his free hand to push the short red skirt over his bare thighs, only slightly covered by thin black lace thigh highs.

Derek moans watching Stiles pull up his thigh highs. They seemed to be inching down his legs and Derek really needed to sober Stiles up. Stiles being this loose because of the alcohol was really going to drive Derek insane.

"You." Stiles slurs, wrapping his arms around Derek’s neck.

"Me?" Derek mocks.

"—Need to carry—hiccup— _me_.”

"That’s not going to happen." Derek scowls down at Stiles and his flailing limbs.

"Oh?" Stiles tried his best to attempt a flirtatious look even though he was completely trashed. Derek stifled a snort.

Before Derek could say anything, Stiles was hopping up onto Derek, climbing his strong body, Stiles’ cloth covered dick face level with his and oh god this was so _not_ happening. Why?

Derek takes Stiles out of there and drives him somewhere to sober him up. Derek took him to a small diner and shoves orange juice and pancakes his way, Stiles eyeing Derek like he’s grown a second head, but in reality, Stiles is just grateful and kind of wondering why Derek is doing this for him.

Even in his slightly drunken hazed mind, he can still tell some things. Like how Derek is really concerned and caring for Stiles’ well being. And he’d noticed this before when they were in the hospital. Derek cares about him. Stiles is still in shock from this revelation to be quite honest. He never thought this day would come. Of all people. _Derek_ Hale. Cares about _Him_.

Stiles catches Derek looking around the diner, he’s got his mouth stuffed full of pancakes and syrup and Derek looks a little fidgety while looking. Curious to see what has Derek’s attention, Stiles looks around and sees people staring at him and Derek and at Stiles’ clothes. Oh shit. He’s wearing a really trashy outfit and it’s Halloween and he probably looks like someone Derek picked up off the street to feed because Derek was a generous soul.

 _This is awkward_.  Stiles thinks, swallowing around the food in his mouth and he thinks it goes down the wrong pipe.

Stiles pats his chest and tries to breathe.

"Are you okay?" Derek asks.

"I’m fine." Stiles cries. The tears in his eyes are a giveaway. "Can we leave. I’m suddenly really uncomfortable."

"Yes we can. Where do you want to go?"

"Can you take me home?" Stiles says.

"Yeah, c’mon." Derek sets a couple dollars on the table for the waitress and then gets up and walks over to Stiles’ side of the booth to help lift him up. He’s still a little wobbly, but he’s sobered up a considerable amount.

Derek walks Stiles to the cashier and pays for the meal and helps Stiles to the door, but Stiles ends up insisting that he walk by himself, pressing his palms against the skirt so it doesn’t ride up. He doesn’t want these strangers to see the lacy red panties that he put on. He didn’t even know why he put those on in the first place, but he likes them.

Derek drives Stiles to his house, the ride is a very quiet one. Derek doesn’t even have music on and Stiles wonders if it’s either because Derek doesn’t like music or if he just wants the quiet right now.

 

~*~

When they finally pull up in front of the Stilinski house, Stiles looks up at the driveway and sees that his Dad’s’ cruiser is still not in the driveway. He must have had a lot of people to deal with. After all, it’s Halloween night and Beacon Hills gets crazy during this night. Stiles sighs, unlocking the door to the Camaro. For some reason he thought that Derek got rid of the Camaro completely, but he’s glad Derek didn’t. He secretly loved the car.

"Do you want me to ugh—help you inside?" Derek tries, blushing a little.

"Um, sure?" Stiles says. Even though he knows he can help himself. He wants to indulge Derek a little. Stiles is enjoying the attention. At least it’s not like the men at the party who were feeling him up and touching his ass. He actually knows Derek. A lot more than Derek probably wanted him to know, but he does. And he likes Derek. _A lot_.

Stiles fumbles for his keys in one of the skirts pockets. Thank fuck the skirt had a pocket. Even though it was extremely small, he managed to fit his phone and his keys. Finding the key that unlocks the front door, Stiles turns the lock and walks in. “Come on in.” Stiles says, making a waving motion for Derek to make himself at home.

Stiles sets the keys in the little bowl next to the couch and flies upstairs to his room.

He thinks Derek follows him, but he’s not sure. It’s not until after he kicks off the heels he was wearing and flops down on the bed on his stomach that he feel’s like someone’s behind him, watching him.

Derek chokes at the sight in front of him. Stiles feels the blush forming on his cheeks and the draft on the back of his thighs. _Oh_ shit.

Derek can see his ass and the outline of his crack through the see through lacy panties. Why does this always _happen_ to him?

Stiles coughs, sitting up on his side, trying to diffuse the situation. “Um—”

"It’s fine, I can leave if you—"

"No, I want you to stay, please." Stiles begs, turning over on his back so he’s not on his side anymore. Stiles flattens the skirt down over his thighs and pats the space next to him for Derek to join him on the bed.

Derek relents and joins him on the bed.

“So,” Stiles starts, looks at Derek for a brief moment before he turns away and runs his fingers over his thighs, “Do you..um.. do you want to do something?”

“Hm?” Derek says, his right hand reaching for Stiles’ skin. Stiles’ breath hitches when Derek touches the inside of his thigh. Derek’s dangerously close to his panty-clothed cock and Stiles wants to moan and scream for Derek to keep going, but he doesn’t know where this _is_ going.

Stiles spread his legs a little more so Derek can have more room to move in between them.

Derek watches Stiles’ face for reactions, breathing heavy, and eyes dilating from lust, his fingers ghosting touches over Stiles’ skin on the inside of his thigh, getting bolder and moving towards his cock.

Derek groans when Stiles’ breath hitches again. He’s clearly found a very erogenous spot. Derek grins to himself, his hand brushing gently over Stiles’ cock and Stiles moans from the touch, clearly not expecting Derek to touch him there so soon.

Stiles doesn’t even know what’s happening or how they got here. He hopes Derek never stops.

Derek moves his hand from between Stiles’ pale legs to grab his hips and move him closer to Derek. Stiles moans when he can feel the warmth practically radiating off of Derek’s body. Was Derek always this strong or is Stiles just extremely horny?

“Oh god.” Stiles whimpers.

Derek’s got his hands caressing Stiles’ face and Stiles is watching him carefully, licking full pink lips in between breathing and moaning. He’s trying not to scream, even though he wants to. Oh how he wants to scream in ecstasy and he hasn’t even come yet.

Derek smirks when Stiles arches back, his beautiful neck on full display for Derek.

Derek grabs Stiles’ cheeks and kisses him. Stiles is taken aback, his eyes still open and processing it, but when Derek starts trying to lick into his mouth, Stiles closes his eyes and opens his mouth for Derek, sucking on his tongue and moaning through the kiss, Stiles’ hands finding their way into Derek’s hair and running his fingers through it.

Stiles pulls back and sighs happily. “Wow, that was..wow.”

"We can stop?" Derek asks, pulling back.

"No." Stiles says, grabbing Derek’s face and wrapping his arms around Derek’s neck, tightly. "Oh god. Why did we never do this before." Stiles moans between the chaste kisses that Derek leaves on his lips. Stiles throws his head to the side, Derek leaning in and licking a white patch of skin that’s dotted with little freckled moles.

"Because you’re a pain in my ass." Derek says simply, smirking when Stiles scowls.

"And you’re an asshole." Stiles moans, pulling Derek’s hair back, so that Derek’s face is away from Stiles’ neck.

Stiles bites his lips when he sees Derek’s eyes flicker to blue and back to hazel. Lust evident in his eyes and Stiles knows this, knows that Derek wants him. Whether it's just to fuck or for real, Stiles doesn’t know, but he knows Derek wants him.

"We need to get this stupid thing off of you," Derek groans, pointing towards the corset Stiles is squished into. It’s red and black, with lots of fabric and lace with little bows.

Stiles nods his head as his reply. Derek’s already moving to rip the thing off of him, but Stiles is trying not to freak out. He’s always thought about what his first time would be like, but thats all it was. Thoughts and imaginations of wild nights in bed with someone.

Now that he’s actually here, he’s nervous as hell. Freaked out beyond compare, because Derek freaking Hale wants him and he’s probably getting fucked tonight. And that scares him, because he wants this. So fucking much.

"Are you okay?" Derek asks, finally having ripped the corset when he could have just untied the laces in the back. Derek’s running his fingers up and down Stiles sides and is thumbing Stiles’ nipples and pinching them in between his fingers.

Stiles can’t stop the hiss that escapes him. “Yes.”

"You’re very sensitive there." Derek groans, his fingernail catching on Stiles’ right nipple, Stiles’ breath hitching and his eyes rolling back briefly before Derek’s grabbing Stiles’ waist and laying him back down on the bed. Derek’s got his hands on the waist of Stiles’ skirt, slowly inching it down Stiles’ waist and thighs. Stiles lifts his back so Derek can inch the skirt the rest of the way down his legs. Derek throws the skirt somewhere in the room, watching Stiles spread out all wanton and laying there with just thigh highs and small red panties on, barely doing anything to cover his flushed cock that’s beading with pre-come.

Derek runs his hands over Stiles’ thighs, thumbs slipping under the black thigh highs and easily removing them. The hairs on Stiles’ legs standing up and Stiles _wants_. Stiles wants Derek to just get on with it, but at the same time he wants this to last. He wants Derek to drag it out and make Stiles writhe and shake from the pleasure of it all.

"Touch me." Stiles breathes, his right hand rubbing circles on Derek’s left arm. Derek’s still wearing too many clothes, he should already be naked by now. Stiles frowns.

"I am." Derek says, moving his hands away from Stiles’ body and towards his own shirt, grabbing the fabric of his shirt at his waist and pulling it up and over his head.

Stiles licks his lips at the sight of Derek’s bare skin. He leans forward to touch Derek again, this time his right pec, his chest is covered in dark hair and Stiles never realized just how much he would like this. “I like you with hair.” Stiles blurts, blushing when he realizes he just said that out loud.

"Oh?" Derek moans, running his hands up and down Stiles’ legs and settling on the band of the panties, tugging gently, carefully. Derek pulls on the panties, pulling them up and over Stiles’ cock and thighs. Stiles hisses.

Stiles blushes when he sees Derek stop and look at him. He’s suddenly really shy and he’s not used to being ogled and looked at the way Derek is looking at him. “Are you—?"

Derek leans down and kisses Stiles on the lips one more time, grabbing Stiles’ thighs and pulling them tight around his waist.

Derek licks into Stiles mouth, hungry and greedy. He wants to devour Stiles whole. Derek grinds his jean clad cock into Stiles groin, the friction causing Stiles to arch his back and groan and cry from it all.

"How far do you want to go?" Derek asks, leaning back, still hovering over Stiles, searching Stiles’ face for an answer.

Stiles inhales sharply before replying, “All the way?”

Derek nods, getting back up to strip off his jeans and briefs.

Before Stiles could say anything about Derek being impossibly ripped, Derek is asking him a question and Stiles has to stop staring at Derek’s cock for a moment to respond.

"Huh?" Stiles asks.

"I said, do you have anything? I can’t fuck you unless you have lube."

"Oh, yeah. There’s a bag next to the lamp on my desk." Stiles says, pointing towards the small bag on his desk.

Derek walks over to the desk and looks through the bag, finding a tube of lube and a small vibe. Derek smirks to himself when he sees it.

Stiles smiles, spreading his legs for Derek, Derek huffs settling in between them and rubbing the back of Stiles’ right thigh to offer comfort.

Derek flips open the cap of the tube and squeezes some of the lube on his fingers, using his left hand to move Stiles legs farther apart, Derek trails his right hand to Stiles’ asshole, fingers catching on Stiles’ rim, not lingering there, but following a path up to his perineum and his balls.

Stiles sucks in a gasp of breath when Derek touches his balls. They’re drawn tight and full.

Derek uses his left hand to rub Stiles’ leg to distract him while he starts to push one finger into Stiles’ hole, slow.

Stiles winces a little, but relaxes his body so it doesn’t hurt as much. It’s not as though it’s the first time he’s been fingered. He’s fingered himself a _lot_ and he knows what he needs to do.

"More." Stiles says, nodding his head to give Derek the go ahead to add another finger.

Derek does so, rubbing along the rim with his thumb before he starts to push in his index finger, to join his middle finger.

"Ahhh." Stiles moans.

"There?"

"Yes. Keep going." Stiles groans.

Derek grabs the tube from his side and adds more lube to his fingers before adding another finger along with the two already inside of Stiles.

Stiles arches his back and yells when Derek’s fingers brush over his prostate briefly.

"Please." Stiles begs, his eyes watering a little.

"What do you need?"

"Are you seriously going to make me say it?" Stiles asks, through clenched teeth.

"No, I just wanted to hear you beg." Derek smiles at Stiles’ indignation.

Stiles huffs. “Fucker.”

Derek laughs.

When Stiles starts to push his body back against Derek’s fingers, Derek stops his movements and Stiles whines.

"Why did you stop?" Stiles asks, his body shaking a little from the stimulation.

"Why do you think?" The question was rhetorical.

Derek grabs the tube of lube one more time and squirts some on his hand to rub on his cock, rubbing it over the head and the shaft, pulling back the foreskin.

Derek holds his cock at Stiles’ hole with his right hand and his left hand is holding Stiles’ right leg at his side to soothe him.

"You know I’m not gonna break, right?" Stiles asks.

"I know," Derek starts, "But I’d rather you be prepared."

Stiles flushes hotly at that.

Stiles nods. Relaxing his body as Derek slowly eases his cock inside Stiles’ warmth.

Derek’s grunts and groans at finally being inside Stiles does little to escape Stiles’ ears.

Once Derek is fully inside Stiles’ body, he starts up a slow rhythm of thrusting in and out and fucking up into Stiles’ sweet spot, head on.

"Fuck!" Stiles curses, trying to grasp onto Derek’s shoulders.

Derek uses his left hand to card Stiles’ right leg over his shoulder so he can thrust faster, pinching Stiles’ nipples and moaning when Stiles bites his lower lip.

Derek runs his right hand up and down Stiles’ abdomen, through Stiles’ happy trail, touching his cock and back up towards Stiles’ nipples, pulling hard on a small pink nub.

Stiles has enough and grabs Derek’s face to kiss him, biting lips and licking at Derek’s stubble. It’s thicker than it was before, but it’s soft and Stiles wants to make a comment about how Derek looks like an old man, a really hot old man, but he decides against it.

Stiles winds his fingers through Derek’s dark hair, running his fingers through and just allows himself to enjoy this. Whatever this is, he’s not sure. Derek’s a mystery that Stiles still wants to solve. He still wants to know everything there is to know about Derek Hale.

Stiles pulls back from the kiss when Derek stops thrusting to look into Derek’s eyes. They’re this odd beautiful mixture of green and so many other colors, Stiles thinks it’s insulting to just call them hazel. They need their own name.

Stiles holds Derek’s cheek, petting the soft hair there, and he swears he sees Derek’s gaze go softer, but he’s probably too far gone with pleasure to tell for sure.

Derek fucks back up into Stiles’ body, leaning in for a kiss, bruising and passionate, licking into Stiles’ mouth, his gums, sucking his tongue. Stiles moans through the kiss.

Who knew kissing Derek Hale would feel so good?

Stiles runs his hands up and down Derek’s shoulder blades, scratching lightly at the skin where Derek’s Triskele tattoo is.

"I’m gonna come." Derek says, his hips pounding into Stiles’ body, Stiles cries from the pressure of Derek’s cock hitting his prostate every time, making him shiver and whine out obscenities.

"Do it!" Stiles moans, eyes closing shut in pleasure, "Fucking come inside me."

Derek looks at Stiles in shock from the words, grabbing Stiles’ cock with his right hand and jerking it, pulling back foreskin and smoothing the pre-come all over Stiles’ shaft, Stiles’ hands grasping Derek’s shoulder and reaching for Derek’s hair to comb his fingers through dark strands.

Derek thrusts one more time before he’s pulsing hard and rough inside Stiles’ warm pliant body.

Grasping Stiles’ cock and rubbing against the dark veins, Stiles screams, hot streams of come splashing against his chest, droplets landing on his neck.

"That was--" Derek says, while coming down from his orgasm.

"Unexpectedly amazing." Stiles finishes for him, sighing softly.

When Derek gets up to grab a towel, Stiles starts to drift off to sleep.

Walking over to the bathroom, Derek grabs a towel and walks back into the bedroom, pulling Stiles' legs apart and wiping his abdomen, neck, thighs and ass, from the sweat and come. After he's done, Derek sets the towel back in the bathroom, washes his hands and goes back to Stiles.

He decides to sit on Stiles' desk chair. It's almost 11:30pm and he wonders if he should leave, let Stiles be by himself, but he also thinks that wouldn't be right. So he stays, watching over Stiles as he sleeps.

 

~*~

When Stiles wakes, it's barely 7am, he notices while looking at his clock next to his bedside, yawning, Stiles stretches his arms. He feels sated and blissful.

He remembers everything, surprisingly. He must have not been that drunk.

"Derek?" Stiles asks, looking around his room, wondering where he's at. He sees Derek by his window, looking outside. The first signs of light appearing in the sky. Did Derek sleep at all?

"Hm?" Derek says, turning away from the window so he's facing Stiles.

Stiles yawns, moving to sit up and stretch his body, the covers of the blanket drifting down his legs as he stands up.

He doesn't feel so shy anymore. He wants to blame it on the losing his 'virginity' part, but he's not so sure. He thinks it’s because he feels so incredibly comfortable around Derek. And it’s taken him quite awhile to feel that way.

Stiles winces when he gets up, feeling a small ache in his ass, grasping his head, Stiles walks over towards the bathroom.

"Your dad is not home yet. Something tells me, he'll probably be back later this morning."

"Oh. Does that mean you're gonna leave?"

"Do you want me to leave?"

“Is it bad if I say no?”

“No, it’s not.” Derek’s lips quirk up in a small smile.

 

~*~

Later when Stiles’ dad gets home, Derek is still in Stiles’ bedroom, getting ready to leave, but before Stiles can try and stop Derek from leaving out the window, the sheriff opens Stiles’ door and stops dead in his tracks.

"Stiles..?" he asks, looking between Derek and Stiles. It’s not as though they’re in some compromising position. Stiles is sitting on the edge of his bed, fully dressed and Derek is standing up near the window. The only thing out of place, are Stiles’ rather provocative Halloween costume pieces laying scattered and ripped around the room.

Derek looks up at the sheriff and then back at Stiles. Stiles is trying not blurt anything out, and Derek looks like he wants to leave to avoid any conversation that is sure to probably land him in jail for the night.

The sheriff sighs, “I’m not even gonna ask. I just want you to be happy, whatever it is that you do or who you choose to be with.”

Stiles’ shocked face doesn’t leave, even when his dad leaves the room, closing the door behind him softly and padding downstairs.

"How do you know we even did anything?" Stiles yells from his bedroom.

"I’m your father, give me more credit than that." the sheriff yells back.

"Oh, damn. He’s got a point." Stiles sighs. Derek nods his head in return.

Before Stiles can say anything else, Derek is kissing him, gripping his face tightly and hungrily licking into Stiles’ mouth, like he wants to devour him whole and Stiles can’t get enough. He wants more, _so_ much more and he’s not sure if Derek would give him that.

Moaning into the kiss and winding his hands around Derek’s neck, Stiles starts to kiss back, biting Derek’s lip and licking his gums, hungry and greedy for everything Derek is willing to give.

Stiles moves back from the kiss, leaning his forehead against Derek’s, breathing hot puffs of air, kiss swollen lips breathe out, “Are we going to talk about last night or—?”

"No…" Derek smiles, strong hands resting at the dip of Stiles’ back, right above Stiles’ ass.

"No?" Stiles repeats, sarcastically.

“No.” Derek repeats, a smirk on his face.

“I want it too, ya know? I want it to happen again. So many times.” Stiles says, casually, looking into Derek’s eyes.

“I do too.”

**Author's Note:**

> thank you for reading!


End file.
